Addition of Chloroprene Grignards to Aromatic Aldehydes: Synthesis of Homoallenyl Alcohols

被引：6

作者：

Geissler, Arne G. A. ^{[1
]}

Breit, Bernhard ^{[1
]}

机构：

[1] Albert Ludwigs Univ Freiburg, Inst Organ Chem, D-79104 Freiburg, Germany

来源：

ORGANIC LETTERS | 2021年 / 23卷 / 07期

关键词：

ALLYLIC ALKYLATION; EFFICIENT SYNTHESIS; CONJUGATE ADDITION; REAGENTS; ALLENES; NUCLEOPHILES; MECHANISM; METAL;

D O I：

10.1021/acs.orglett.1c00527

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A general procedure for the one-pot synthesis of racemic homoallenyl alcohols from the corresponding aldehyde and chloroprene-derived Grignards is described. Employing bis[2-dimethylaminoethyl]ether (BDMAEE) as an additive at low temperatures shifts the selectivity of the chloroprene Grignard addition to aldehydes such that it is almost exclusive toward allene formation. In a set of follow-up experiments, simple and more elaborate methods for further derivatization have been demonstrated, allowing quick access to more complex structures.

引用

页码：2621 / 2625

页数：5

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